N-phthalyl-4-fluoro-4-carboxyglutamic acid, α-methyl ester | 133384-83-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-phthalyl-4-fluoro-4-carboxyglutamic acid, α-methyl ester
• 英文别名: 2-[2-(1,3-Dioxoisoindol-2-yl)-3-methoxy-3-oxopropyl]-2-fluoropropanedioic acid
• CAS: 133384-83-5
• 化学式: C₁₅H₁₂FNO₈
• 分子量: 353.261
• InChiKey: QHHGNHCRBYPHJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-phthalyl-4-fluoro-4-carboxyglutamic acid, α-methyl ester 在 盐酸 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 4-fluoro-5,5'-dihydroxy-leucine
  参考文献：
  名称：

  Synthesis of 5,5′-dihydroxyleucine and 4-fluoro 5,5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids

  摘要：

  Schemes for the synthesis of 5-5'-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable ''aminoacid moiety'' with 2,2-dimethyl-5-iodomethyl-1,3-dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N-diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, which could be prepared by reduction of a suitably protected 4-fluoro-4-carboxyglutamate with BMS.

  DOI：

  10.1016/s0040-4020(01)80939-x
• 作为产物：
  描述：

  N-phthalyl-4-fluoro-4-benzyloxycarbonyl-glutamic acid, α-methyl, γ-benzyl diester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 以90%的产率得到N-phthalyl-4-fluoro-4-carboxyglutamic acid, α-methyl ester
  参考文献：
  名称：

  Synthesis of 5,5′-dihydroxyleucine and 4-fluoro 5,5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids

  摘要：

  Schemes for the synthesis of 5-5'-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable ''aminoacid moiety'' with 2,2-dimethyl-5-iodomethyl-1,3-dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N-diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, which could be prepared by reduction of a suitably protected 4-fluoro-4-carboxyglutamate with BMS.

  DOI：

  10.1016/s0040-4020(01)80939-x

文献信息

• Synthesis of 5,5′-dihydroxyleucine and 4-fluoro 5,5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids
  作者：Joëlle Dubois、Christine Fourès、Sonia Bory、Serge Falcou、Michel Gaudry、Andrée Marquet

  DOI：10.1016/s0040-4020(01)80939-x

  日期：1991.1

  Schemes for the synthesis of 5-5'-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable ''aminoacid moiety'' with 2,2-dimethyl-5-iodomethyl-1,3-dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N-diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, which could be prepared by reduction of a suitably protected 4-fluoro-4-carboxyglutamate with BMS.